(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine → (S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline

HRID 2404885Notes

Reaction equation

HRID 2404885 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:8]=1>[Pd]>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:16]([F:18])([F:17])[F:19])[CH:8]=1

Participants

3

Reactant 1

HCID 59395009(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine

Product 1

HCID 59395038(S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (2.45 g, 8.9 mmol) and palladium on carbon (245 mg, 10 wt %) was flushed with N2 followed by evacuating under vacuum. Methanol (15 mL) was added under inert atmosphere followed by evacuating under vacuum. The reaction mixture was stirred overnight under an atmosphere of H2. The palladium catalyst was removed by filtration and solvent was removed under reduced pressure to give (S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ 6.78 (d, J=8.8 Hz, 1H), 6.70-6.67 (m, 1H), 6.47 (d, J=2.7 Hz, 1H), 4.68 (s, 2H), 3.76-3.69 (m, 1H), 3.32-3.27 (m, 1H), 3.02-2.96 (m, 1H), 2.05-1.94 (m, 2H), 1.93-1.84 (m, 1H), 1.64-1.58 (m, 1H), 1.05 (d, J=6.1 Hz, 3H). LC/MS: m/z 245.1 (M+H)+ at 0.48 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas flushed with N2
  2. customby evacuating under vacuum
  3. additionMethanol (15 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. customThe palladium catalyst was removed by filtration and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-13227310f55d41459f4dab45bea11d57
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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